Kathryn makes a bet that her step-brother, Sebastian, won't be able to bed Annette (a virgin, who wants to wait until marriage) before the start of the school year. If he loses, Kathryn gets his Roadster, if he wins, he gets Kathryn (Scott Stoecker)

Kathryn and Sebastian, two wealthy, manipulative teenage step-siblings from Manhattan's upper-crust, conspire in Cruel Intentions, a wickedly entertaining tale of seduction and betrayal. The stakes are high when the duo agrees upon a deliciously diabolical wager of sexual conquest without consequences. The pawns? The naive Celcile Caldwell and the virginal Annette Hargrove. Its summer break, and Kathryn has been dumped by her beau, Court Reynolds, for the innocent Cecile. Desperate to get even, Kathryn challenges Sebastian to ruin Celcile by deflowering her and turning her into a tramp-thus humiliating Court by delivering Cecile to him as damaged goods. Sebastian has pretty much 'had' all of the girls in New York City up to this point, and he's gotten a bit bored of it all. Though this is too easy a conquest for him, he obliges. He sets his sights on a greater challenge-the new headmaster's daughter, Annette, who recently wrote an article in Seventeen Magazine about how she intends to stay pure until she marries her boyfriend. Sebastian bets Kathryn that he can seduce the chaste and pristine Annette before school begins in the fall. Kathryn thinks this feat impossible and quickly agrees to the wager. The stakes: if Sebastian succeeds, Kathryn must give him a night of unbridled pleasure, something's he's wanted since their parents got married. If he fails, he must forfeit his priceless 1956 Jaguar to Kathryn and suffer the shame of defeat. (--)

Bickering step-siblings together quietly control much of the social lives of the students in an affluent NY prep school. Sebastian sees himself as a kind of Don Juan, who always gets his woman, while Katherine would rather enact revenge on ex-flames and corrupt incoming freshmen. One day, Kathryn and Sebastian, driven by a mutual lust for each other and a love of messing with innocent young people's lives, hatch a nefarious plan, and place a kind of bet. Sebastian is to woo and bed the daughter of the new headmaster (a very adamant virgin with plans to only "wait until marriage"), and if he is able to accomplish this seemingly impossible task, he can have his way with Kathryn - the one woman whom he KNOWS he can not have. If he is unable to seduce the ice queen, however, Katherine gets his classic car. (J.J. Neal)

A pair of unscrupulous siblings star in a sexy tale of seduction, revenge and conquest. After cleverly seducing and ruining the reputation of an unsuspecting classmate, the sparks fly when Kathryn poses the ultimate challenge to her insatiable stepbrother Sebastian: deflower the Headmaster's beautiful, virgin daughter Annette. If he fails, Kathryn gets his 1956 jaguar convertible, but if he succeeds, Sebastain gets to possess and bed Kathryn. The stakes are high, but for Sebastian, the payoff is feverishly irresistible and before the summer's over, no one will escape their relentless game of cat and mouse . . . until one of them is bitten by the most unlikely sensation of all . . . love. (Robert Lynch)

Sarah Michelle Gellar and Ryan Phillippe sizzle as a pair of unscrupulous siblings in a deliciously sexy tale of seduction, revenge and conquest. After cleverly seducing and ruining the reputation of an unsuspecting classmate (Selma Blair, Can't Hardly Wait), the sparks fly when Kathryn (Gellar) poses the ultimate challenge to her insatiable stepbrother Sebastian (Phillippe): deflower the Headmaster's beautiful, virgin daughter Annette (Reese Witherspoon). If he fails, Kathryn gets his most prized possession, but if hesucceeds, Sebastian gets to possess and bed Kathryn. The stakes are high, but for Sebastian, the payoff is feverishly irresistible and before the summer's over, no one will escape their relentless game of cat and mouse until one of them is bitten by the most unlikely sensation of all ...love. (Amazon.com)

Ryan Phillippe and Sarah Michelle Gellar play bickering step-siblings who, together, quietly control much of the social lives of the students in an affluent NY prep school. Phillippe's Sebastian sees himself as a kind of Don Juan, who always gets his woman, while Gellar's Katherine would rather enact revenge on ex-flames and corrupt incoming freshmen. One day, Kathryn and Sebastian, driven by a mutual lust for each other and a love of messing with innocent young people's lives, hatch a nefarious plan, and place a kind of bet. Sebastian is to woo and bed the daughter of the new headmaster (Reese Witherspoon, playing a very adamant virgin with plans to only "wait until marriage"), and if he is able to accomplish this seemingly impossible task, he can have his way with Gellar - the one woman whom he KNOWS he can not have. If he is unable to seduce the ice queen, however, Katherine gets his classic car. (Amazon.com)

This modern-day teen update of Les Liaisons Dangereuses suffered at the hands of both critics and moviegoers thanks to its sumptuous ad campaign, which hyped the film as an arch, highly sexual, faux-serious drama (not unlike the successful, Oscar-nominated Dangerous Liaisons). In fact, this intermittently successful sudser plays like high comedy for its first two-thirds, as its two evil heroes, rich stepsiblings Kathryn (Sarah Michelle Gellar) and Sebastian (Ryan Phillippe), blithely ruin lives and reputations with hearts as black as coal. Kathryn wants revenge on a boyfriend who dumped her, so she befriends his new intended, the gawky Cecile (Selma Blair), and gets Sebastian to deflower the innocent virgin. The meat of the game, though, lies in Sebastian's seduction of good girl Annette (a down-to-earth Reese Witherspoon), who's written a nationally published essay entitled "Why I Choose to Wait." If he fails, Kathryn gets his precious vintage convertible; if he wins, he gets Kathryn--in the sack. When the movie sticks to the merry ruination of Kathryn and Sebastian's pawns, it's highly enjoyable: Gellar in particular is a two-faced manipulator extraordinaire, and Phillippe, usually a black hole, manages some fun as a hipster Eurotrash stud. Most pleasantly surprising of all is Witherspoon, who puts a remarkably self-assured spin on a character usually considered vulnerable and tortured (see Michelle Pfeiffer in Dangerous Liaisons). Unfortunately, writer-director Roger Kumble undermines everything he's built up with a false ending that's true to neither the reconceived characters nor the original story--revenge is a dish best served cold, not cooked up with unnecessary plot twists. (Mark Englehart, Amazon.com)